1,2,4-Trioxane
Encyclopedia
1,2,4-Trioxane is one of the isomers of trioxane
Trioxane
Trioxane refers to a pair of isomeric organic compounds having the molecular formula C3H6O3. Each contains a six membered ring with three carbon atoms and three oxygen atoms.The two isomers are...

. It has the molecular formula C3H6O3 and consists of a six membered ring with three carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 atoms and three oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...

 atoms. The two adjacent oxygen atoms form a peroxide
Organic peroxide
Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...

 functional group and the other forms an ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

 functional group. It is a cyclic acetal
Acetal
An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...

 with one of the oxygen atoms in the acetal group being in a peroxide group.

1,2,4-Trioxane itself has not been isolated or characterized, but rather only studied computationally. However, it constitutes an important structural element of some more complex organic compounds. The natural compound artemisinin
Artemisinin
Artemisinin , also known as Qinghaosu , and its derivatives are a group of drugs that possess the most rapid action of all current drugs against falciparum malaria. Treatments containing an artemisinin derivative are now standard treatment worldwide for falciparum malaria...

, isolated from the sweet wormwood plant (Artemisia annua
Artemisia annua
Artemisia annua, also known as Sweet Wormwood, Sweet Annie, Sweet Sagewort or Annual Wormwood , is a common type of wormwood that is native to temperate Asia, but naturalized throughout the world.-Characteristics:...

), and some semi-synthetic derivatives are important antimalarial drug
Antimalarial drug
Antimalarial medications, also known as antimalarials, are designed to prevent or cure malaria. Such drugs may be used for some or all of the following:* Treatment of malaria in individuals with suspected or confirmed infection...

s. Completely synthetic analogs containing the 1,2,4-trioxane ring are important potential improvements over the naturally derived artemisinins. The peroxide group in the 1,2,4-trioxane core of artemisinin is cleaved
Bond cleavage
Bond cleavage, or scission, is the splitting of chemical bonds.If the two electrons in a cleaved covalent bond are divided between the products, the process is known as homolytic fission and free redicals are generated by homolytic cleavage the process is known as homolytic fission or homolysis...

 in the presence of the malaria parasite leading to reactive oxygen
Reactive oxygen species
Reactive oxygen species are chemically reactive molecules containing oxygen. Examples include oxygen ions and peroxides. Reactive oxygen species are highly reactive due to the presence of unpaired valence shell electrons....

 radicals
Radical (chemistry)
Radicals are atoms, molecules, or ions with unpaired electrons on an open shell configuration. Free radicals may have positive, negative, or zero charge...

that are damaging to the parasite.
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